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id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Drug_interactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Drug_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Drug interactions</span> </div> </a> <ul id="toc-Drug_interactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Available forms</span> </div> </a> <button aria-controls="toc-Available_forms-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Available forms subsection</span> </button> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> <li id="toc-Combination" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Combination"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Combination</span> </div> </a> <ul id="toc-Combination-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" 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Available in 25 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-25" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">25 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%84%D9%88%D9%83%D9%84%D9%88%D9%83%D8%B2%D8%A7%D8%B3%D9%8A%D9%84%D9%8A%D9%86" title="فلوكلوكزاسيلين – Arabic" lang="ar" hreflang="ar" data-title="فلوكلوكزاسيلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D9%84%D9%88%DA%A9%D9%84%D9%88%D9%82%D8%B2%D8%A7%D8%B3%DB%8C%D9%84%DB%8C%D9%86" title="فلوکلوقزاسیلین – South Azerbaijani" lang="azb" hreflang="azb" data-title="فلوکلوقزاسیلین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A7%8D%E0%A6%B2%E0%A7%81%E0%A6%95%E0%A7%8D%E0%A6%B2%E0%A6%95%E0%A7%8D%E0%A6%B8%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%B2%E0%A6%BF%E0%A6%A8" title="ফ্লুক্লক্সাসিলিন – Bangla" lang="bn" hreflang="bn" data-title="ফ্লুক্লক্সাসিলিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Flucloxacil%C2%B7lina" title="Flucloxacil·lina – Catalan" lang="ca" hreflang="ca" data-title="Flucloxacil·lina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Flucloxacillin" title="Flucloxacillin – Danish" lang="da" hreflang="da" data-title="Flucloxacillin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Flucloxacillin" title="Flucloxacillin – German" lang="de" hreflang="de" data-title="Flucloxacillin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Flucloxacilina" title="Flucloxacilina – Spanish" lang="es" hreflang="es" data-title="Flucloxacilina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%84%D9%88%DA%A9%D9%84%D9%88%DA%AF%D8%B2%D8%A7%D8%B3%DB%8C%D9%84%DB%8C%D9%86" title="فلوکلوگزاسیلین – Persian" lang="fa" hreflang="fa" data-title="فلوکلوگزاسیلین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Flucloxacilline" title="Flucloxacilline – French" lang="fr" hreflang="fr" data-title="Flucloxacilline" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Flukloksasilin" title="Flukloksasilin – Indonesian" lang="id" hreflang="id" data-title="Flukloksasilin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Flucloxacillina" title="Flucloxacillina – Italian" lang="it" hreflang="it" data-title="Flucloxacillina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%9C%D7%95%D7%A7%D7%9C%D7%95%D7%A7%D7%A1%D7%A6%D7%99%D7%9C%D7%99%D7%9F" title="פלוקלוקסצילין – Hebrew" lang="he" hreflang="he" data-title="פלוקלוקסצילין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Flucloxacilline" title="Flucloxacilline – Dutch" lang="nl" hreflang="nl" data-title="Flucloxacilline" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%83%AB%E3%82%AF%E3%83%AD%E3%82%AD%E3%82%B5%E3%82%B7%E3%83%AA%E3%83%B3" title="フルクロキサシリン – Japanese" lang="ja" hreflang="ja" data-title="フルクロキサシリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AB%E0%AD%8D%E0%AC%B2%E0%AD%81%E0%AC%95%E0%AD%8D%E0%AC%B2%E0%AD%8B%E0%AC%95%E0%AD%8D%E0%AC%B8%E0%AC%BE%E0%AC%B8%E0%AC%BF%E0%AC%B2%E0%AC%BF%E0%AC%A8" title="ଫ୍ଲୁକ୍ଲୋକ୍ସାସିଲିନ – Odia" lang="or" hreflang="or" data-title="ଫ୍ଲୁକ୍ଲୋକ୍ସାସିଲିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Flukloksacylina" title="Flukloksacylina – Polish" lang="pl" hreflang="pl" data-title="Flukloksacylina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Flucloxacilina" title="Flucloxacilina – Portuguese" lang="pt" hreflang="pt" data-title="Flucloxacilina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Flucloxacilin%C4%83" title="Flucloxacilină – Romanian" lang="ro" hreflang="ro" data-title="Flucloxacilină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Flucloxacillin" title="Flucloxacillin – Albanian" lang="sq" hreflang="sq" data-title="Flucloxacillin" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Flukloksacilin" title="Flukloksacilin – Slovenian" lang="sl" hreflang="sl" data-title="Flukloksacilin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D0%BB%D1%83%D0%BA%D0%BB%D0%BE%D0%BA%D1%81%D0%B0%D1%86%D0%B8%D0%BB%D0%B8%D0%BD" title="Флуклоксацилин – Serbian" lang="sr" hreflang="sr" data-title="Флуклоксацилин" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Flukloksacilin" title="Flukloksacilin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Flukloksacilin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Flukloxacillin" title="Flukloxacillin – Swedish" lang="sv" hreflang="sv" data-title="Flukloxacillin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Flukloksasilin" title="Flukloksasilin – Turkish" lang="tr" hreflang="tr" data-title="Flukloksasilin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%B0%9F%E6%B0%AF%E8%A5%BF%E6%9E%97" title="氟氯西林 – Chinese" lang="zh" hreflang="zh" data-title="氟氯西林" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q1994556#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit 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data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Flucloxacillin">Flucloxacillin</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Flucloxacillin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Flucloxacillin.svg/220px-Flucloxacillin.svg.png" decoding="async" width="220" height="194" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Flucloxacillin.svg/330px-Flucloxacillin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Flucloxacillin.svg/440px-Flucloxacillin.svg.png 2x" data-file-width="512" data-file-height="451" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Flucloxacillin-from-xtal-1980-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Flucloxacillin-from-xtal-1980-3D-balls.png/220px-Flucloxacillin-from-xtal-1980-3D-balls.png" decoding="async" width="220" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Flucloxacillin-from-xtal-1980-3D-balls.png/330px-Flucloxacillin-from-xtal-1980-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Flucloxacillin-from-xtal-1980-3D-balls.png/440px-Flucloxacillin-from-xtal-1980-3D-balls.png 2x" data-file-width="1100" data-file-height="774" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Floxapen, others<sup id="cite_ref-Drugs.com_1-0" class="reference"><a href="#cite_note-Drugs.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">BRL-2039</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/flucloxacillin.html">International Drug Names</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> B1</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a>, <a href="/wiki/Intrapleural" class="mw-redirect" title="Intrapleural">intrapleural</a>, <a href="/wiki/Intraarticular" class="mw-redirect" title="Intraarticular">intraarticular</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_J01" title="ATC code J01">J01CF05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01CF05">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-EMA2020_4-0" class="reference"><a href="#cite_note-EMA2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">50–70%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">0.75–1 hour<sup id="cite_ref-Hitchings2015_5-0" class="reference"><a href="#cite_note-Hitchings2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a><sup id="cite_ref-Hitchings2015_5-1" class="reference"><a href="#cite_note-Hitchings2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(2<i>S</i>,5<i>R</i>,6<i>R</i>)-6-({[3-(2-chloro-5-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5250-39-5">5250-39-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/21319">21319</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div 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class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8023056">DTXSID8023056</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q1994556#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.023.683">100.023.683</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q1994556#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>19</sub><span title="Hydrogen">H</span><sub>17</sub><span title="Chlorine">Cl</span><span title="Fluorine">F</span><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span><sub>5</sub><span title="Sulfur">S</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002453870000000000♠"></span>453.87</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29%5BC%40%40H%5D3N4C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29c2c%28onc2c1c%28F%29cccc1Cl%29C%29%5BC%40H%5D4SC3%28C%29C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(F)cccc1Cl)C)[C@H]4SC3(C)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:UIOFUWFRIANQPC-JKIFEVAISA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=461101078&page2=Flucloxacillin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Flucloxacillin</b>, also known as <b>floxacillin</b>, is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> used to treat <a href="/wiki/Skin_infections" class="mw-redirect" title="Skin infections">skin infections</a>, <a href="/wiki/Otitis_externa" title="Otitis externa">external ear infections</a>, infections of leg ulcers, diabetic foot infections, and <a href="/wiki/Osteomyelitis" title="Osteomyelitis">infection of bone</a>.<sup id="cite_ref-BNF80_6-0" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It may be used together with other medications to treat <a href="/wiki/Pneumonia" title="Pneumonia">pneumonia</a>, and <a href="/wiki/Endocarditis" title="Endocarditis">endocarditis</a>.<sup id="cite_ref-BNF80_6-1" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It may also be used prior to surgery to prevent <i><a href="/wiki/Staphylococcus" title="Staphylococcus">Staphylococcus</a></i> infections.<sup id="cite_ref-BNF80_6-2" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is not effective against <a href="/wiki/Methicillin-resistant_Staphylococcus_aureus" title="Methicillin-resistant Staphylococcus aureus">methicillin-resistant <i>Staphylococcus aureus</i></a> (MRSA).<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It is taken by mouth or given by injection into a vein or muscle.<sup id="cite_ref-BNF80_6-3" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects include an upset stomach.<sup id="cite_ref-BNF80_6-4" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Other side effects may include muscle or joint pains, shortness of breath, and liver problems.<sup id="cite_ref-BNF80_6-5" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wu2011_8-0" class="reference"><a href="#cite_note-Wu2011-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It appears to be safe during pregnancy and breastfeeding.<sup id="cite_ref-BNF80_6-6" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It should not be used in those who are allergic to <a href="/wiki/Penicillin" title="Penicillin">penicillin</a>.<sup id="cite_ref-BNF80_6-7" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Narrow-spectrum_antibiotic" title="Narrow-spectrum antibiotic">narrow-spectrum</a> <a href="/wiki/Beta-lactam_antibiotic" class="mw-redirect" title="Beta-lactam antibiotic">beta-lactam antibiotic</a> of the <a href="/wiki/Penicillin" title="Penicillin">penicillin</a> class.<sup id="cite_ref-Wu2011_8-1" class="reference"><a href="#cite_note-Wu2011-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is similar in effect to <a href="/wiki/Cloxacillin" title="Cloxacillin">cloxacillin</a> and <a href="/wiki/Dicloxacillin" title="Dicloxacillin">dicloxacillin</a>, being active against <a href="/wiki/Penicillinase" class="mw-redirect" title="Penicillinase">penicillinase</a> forming bacteria.<sup id="cite_ref-Weller2014_9-0" class="reference"><a href="#cite_note-Weller2014-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Flucloxacillin was patented in 1961.<sup id="cite_ref-Alapi2006_10-0" class="reference"><a href="#cite_note-Alapi2006-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is not commonly used in the United States or Canada as of 2011.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Flucloxacillin is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> used to treat <a href="/wiki/Skin_infections" class="mw-redirect" title="Skin infections">skin infections</a>, <a href="/wiki/Otitis_externa" title="Otitis externa">external ear infections</a>, infections of leg ulcers, <a href="/wiki/Diabetic_foot_infection" title="Diabetic foot infection">diabetic foot infections</a>, and <a href="/wiki/Osteomyelitis" title="Osteomyelitis">infection of bone</a>.<sup id="cite_ref-BNF80_6-8" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Skin">Skin</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=2" title="Edit section: Skin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Flucloxacillin is used for both <a href="/wiki/Staphylococcal" class="mw-redirect" title="Staphylococcal">staphylococcal</a> and <a href="/wiki/Streptococcal" class="mw-redirect" title="Streptococcal">streptococcal</a> skin infections.<sup id="cite_ref-Stanway_12-0" class="reference"><a href="#cite_note-Stanway-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> These include <a href="/wiki/Folliculitis" title="Folliculitis">folliculitis</a>, <a href="/wiki/Carbuncles" class="mw-redirect" title="Carbuncles">carbuncles</a>,<sup id="cite_ref-Gould2016_13-0" class="reference"><a href="#cite_note-Gould2016-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Impetigo" title="Impetigo">impetigo</a>, <a href="/wiki/Ecthyma" title="Ecthyma">ecthyma</a>, <a href="/wiki/Cellulitis" title="Cellulitis">cellulitis</a>, <a href="/wiki/Erysipelas" title="Erysipelas">erysipelas</a>, <a href="/wiki/Necrotising_fasciitis" class="mw-redirect" title="Necrotising fasciitis">necrotising fasciitis</a>, and infections of skin conditions such as <a href="/wiki/Eczema" class="mw-redirect" title="Eczema">eczema</a>, <a href="/wiki/Scabies" title="Scabies">scabies</a>, ulcers and <a href="/wiki/Acne" title="Acne">acne</a>.<sup id="cite_ref-BNF80_6-9" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Stanway_12-1" class="reference"><a href="#cite_note-Stanway-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EMC125_14-0" class="reference"><a href="#cite_note-EMC125-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Due to the widespread belief that dual-therapy is needed to cover both <i>Staphylococcus</i> and <i>Streptococcus</i> in cellulitis, flucloxacillin is sometimes given with the addition of <a href="/wiki/Benzylpenicillin" title="Benzylpenicillin">benzylpenicillin</a> for more severe cellulitis.<sup id="cite_ref-Hitchings2015_5-2" class="reference"><a href="#cite_note-Hitchings2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> However, support for this practice has lessened since findings in a study published in the <i><a href="/wiki/Emergency_Medicine_Journal" title="Emergency Medicine Journal">Emergency Medicine Journal</a></i> in 2005 did not show this combination to give additional clinical benefit.<sup id="cite_ref-Leman2005_15-0" class="reference"><a href="#cite_note-Leman2005-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sark2011_16-0" class="reference"><a href="#cite_note-Sark2011-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cox2009_17-0" class="reference"><a href="#cite_note-Cox2009-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> In the UK, using flucloxacillin alone is the first choice for treating cellulitis. Some other countries vary.<sup id="cite_ref-Sullivan2018_18-0" class="reference"><a href="#cite_note-Sullivan2018-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 142.66666666667px"> <div class="thumb" style="width: 140.66666666667px;"><span typeof="mw:File"><a href="/wiki/File:Impetigo2020.jpg" class="mw-file-description" title="Impetigo"><img alt="Impetigo" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Impetigo2020.jpg/211px-Impetigo2020.jpg" decoding="async" width="141" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Impetigo2020.jpg/316px-Impetigo2020.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Impetigo2020.jpg/421px-Impetigo2020.jpg 2x" data-file-width="2673" data-file-height="2285" /></a></span></div> <div class="gallerytext">Impetigo</div> </li> <li class="gallerybox" style="width: 128.66666666667px"> <div class="thumb" style="width: 126.66666666667px;"><span typeof="mw:File"><a href="/wiki/File:Facial_erysipelas.jpg" class="mw-file-description" title="Erysipelas"><img alt="Erysipelas" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Facial_erysipelas.jpg/250px-Facial_erysipelas.jpg" decoding="async" width="127" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Facial_erysipelas.jpg/330px-Facial_erysipelas.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Facial_erysipelas.jpg/500px-Facial_erysipelas.jpg 2x" data-file-width="2127" data-file-height="2013" /></a></span></div> <div class="gallerytext">Erysipelas</div> </li> <li class="gallerybox" style="width: 162px"> <div class="thumb" style="width: 160px;"><span typeof="mw:File"><a href="/wiki/File:Folliculitis2.jpg" class="mw-file-description" title="Folliculitis"><img alt="Folliculitis" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Folliculitis2.jpg/240px-Folliculitis2.jpg" decoding="async" width="160" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Folliculitis2.jpg/360px-Folliculitis2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Folliculitis2.jpg/480px-Folliculitis2.jpg 2x" data-file-width="3648" data-file-height="2736" /></a></span></div> <div class="gallerytext">Folliculitis</div> </li> <li class="gallerybox" style="width: 162px"> <div class="thumb" style="width: 160px;"><span typeof="mw:File"><a href="/wiki/File:Cellulitis1.jpg" class="mw-file-description" title="Cellulitis"><img alt="Cellulitis" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Cellulitis1.jpg/250px-Cellulitis1.jpg" decoding="async" width="160" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Cellulitis1.jpg/500px-Cellulitis1.jpg 1.5x" data-file-width="1632" data-file-height="1224" /></a></span></div> <div class="gallerytext">Cellulitis</div> </li> <li class="gallerybox" style="width: 162px"> <div class="thumb" style="width: 160px;"><span typeof="mw:File"><a href="/wiki/File:Carbuncle.jpg" class="mw-file-description" title="Carbuncle"><img alt="Carbuncle" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Carbuncle.jpg/240px-Carbuncle.jpg" decoding="async" width="160" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Carbuncle.jpg/360px-Carbuncle.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Carbuncle.jpg/480px-Carbuncle.jpg 2x" data-file-width="4624" data-file-height="3468" /></a></span></div> <div class="gallerytext">Carbuncle</div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Wounds">Wounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=3" title="Edit section: Wounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Infections of leg ulcers can be treated with flucloxacillin.<sup id="cite_ref-BNF80_6-10" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> With diabetic foot infections the dose is adjusted according to whether the infection appears mild, moderate or severe.<sup id="cite_ref-BNF80_6-11" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bone">Bone</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=4" title="Edit section: Bone"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Despite having a lower than optimum drug penetration into bone ratio of 10–20%, flucloxacillin appears effective in treating <a href="/wiki/Osteomyelitis" title="Osteomyelitis">osteomyelitis</a>.<sup id="cite_ref-Preiss2020_19-0" class="reference"><a href="#cite_note-Preiss2020-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Depending on local guidance it may be used in the treatment of <a href="/wiki/Septic_arthritis" title="Septic arthritis">infection of joints</a> while waiting for culture results.<sup id="cite_ref-Hitchings2015_5-3" class="reference"><a href="#cite_note-Hitchings2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KumarClark2011_21-0" class="reference"><a href="#cite_note-KumarClark2011-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=5" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It may be used in combination with other antibiotics to treat <a href="/wiki/Pneumonia" title="Pneumonia">pneumonia</a> and can be used to prevent infection before surgery, particularly heart, lung, or bone surgery.<sup id="cite_ref-BNF80_6-12" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EMC125_14-1" class="reference"><a href="#cite_note-EMC125-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> When used to treat <a href="/wiki/Endocarditis" title="Endocarditis">endocarditis</a>, in combination with other antibiotics or alone, the dose of flucloxacillin may need to exceed the usual dose.<sup id="cite_ref-BNF80_6-13" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Resistance">Resistance</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=6" title="Edit section: Resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Despite flucloxacillin being insensitive to beta-lactamases, some organisms have developed resistance to it and other narrow-spectrum β-lactam antibiotics including <a href="/wiki/Methicillin" title="Methicillin">methicillin</a>. Such organisms include <a href="/wiki/Methicillin-resistant_Staphylococcus_aureus" title="Methicillin-resistant Staphylococcus aureus">methicillin-resistant <i>Staphylococcus aureus</i></a>, which has developed resistance to flucloxacillin and other penicillins by having an altered penicillin-binding protein.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=7" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common side effects associated with the use of flucloxacillin include: <a href="/wiki/Diarrhoea" class="mw-redirect" title="Diarrhoea">diarrhoea</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Rash" title="Rash">rash</a>, <a href="/wiki/Urticaria" class="mw-redirect" title="Urticaria">urticaria</a>, <a href="/wiki/Pain" title="Pain">pain</a> and <a href="/wiki/Inflammation" title="Inflammation">inflammation</a> at injection site, <a href="/wiki/Superinfection" title="Superinfection">superinfection</a> (including <a href="/wiki/Candidiasis" title="Candidiasis">candidiasis</a>), <a href="/wiki/Allergy" title="Allergy">allergy</a>, and transient increases in liver enzymes and bilirubin.<sup id="cite_ref-AMH2006_23-0" class="reference"><a href="#cite_note-AMH2006-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Rarely, in fewer than 1 in 1,000 people, <a href="/wiki/Cholestasis" title="Cholestasis">cholestatic jaundice</a> (also referred to as cholestatic hepatitis) has been associated with flucloxacillin therapy. It may appear as pale stool with dark urine, and yellowish eyes and skin.<sup id="cite_ref-NHS_24-0" class="reference"><a href="#cite_note-NHS-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The reaction may occur up to several weeks after treatment has stopped, and takes weeks to resolve. The estimated incidence is one in 15,000 exposures, and is more frequent in people over the age of 55, females, and those with a treatment duration of longer than two weeks.<sup id="cite_ref-BNF80_6-14" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NHS_24-1" class="reference"><a href="#cite_note-NHS-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AMH2006_23-1" class="reference"><a href="#cite_note-AMH2006-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Flucloxacillin is contraindicated in those with a previous history of allergy to penicillins, <a href="/wiki/Cephalosporin" title="Cephalosporin">cephalosporins</a>, or <a href="/wiki/Carbapenem" title="Carbapenem">carbapenems</a>. It should also not be used in the eye, or administered to those with a history of <a href="/wiki/Cholestasis" title="Cholestasis">cholestatic hepatitis</a> associated with the use of dicloxacillin or flucloxacillin.<sup id="cite_ref-AMH2006_23-2" class="reference"><a href="#cite_note-AMH2006-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>It should be used with caution in the elderly, patients with renal impairment where a reduced dose is required, and those with hepatic impairment, due to the risk of cholestatic hepatitis.<sup id="cite_ref-AMH2006_23-3" class="reference"><a href="#cite_note-AMH2006-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>It should be taken on an empty stomach, one half to one hour before food, as absorption is reduced when taken with food,<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> though some studies suggest that this does not compromise flucloxacillin plasma concentrations in most circumstances.<sup id="cite_ref-US_National_Library_of_Medicine_26-0" class="reference"><a href="#cite_note-US_National_Library_of_Medicine-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>The UK's <a href="/wiki/National_Health_Service" title="National Health Service">National Health Service</a> recommends taking at least 30 minutes before food and at least 2 hours after.<sup id="cite_ref-NHS_24-2" class="reference"><a href="#cite_note-NHS-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Drug_interactions">Drug interactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=8" title="Edit section: Drug interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Flucloxacillin can reduce the excretion of <a href="/wiki/Methotrexate" title="Methotrexate">methotrexate</a>, potentially resulting in a risk of methotrexate toxicity. The level of flucloxacillin in the blood may rise in kidney failure and with the use of <a href="/wiki/Probenecid" title="Probenecid">probenecid</a>.<sup id="cite_ref-Weller2014_9-1" class="reference"><a href="#cite_note-Weller2014-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=9" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Beta-lactam_antibiotic" class="mw-redirect" title="Beta-lactam antibiotic">Beta-lactam antibiotic</a></div> <p>Flucloxacillin is a <a href="/wiki/Narrow-spectrum_antibiotic" title="Narrow-spectrum antibiotic">narrow-spectrum</a> <a href="/wiki/Beta-lactam_antibiotic" class="mw-redirect" title="Beta-lactam antibiotic">antibiotic</a> belonging to the <a href="/wiki/Penicillin" title="Penicillin">penicillin</a> group of <a href="/wiki/Antibiotic" title="Antibiotic">antibiotics</a>.<sup id="cite_ref-Wu2011_8-2" class="reference"><a href="#cite_note-Wu2011-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NIH1_27-0" class="reference"><a href="#cite_note-NIH1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> It works by breaking down the bacterial cell wall.<sup id="cite_ref-NIH1_27-1" class="reference"><a href="#cite_note-NIH1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Like other β-lactam antibiotics, flucloxacillin <a href="/wiki/Mechanism_of_action" title="Mechanism of action">acts</a> by inhibiting the synthesis of bacterial <a href="/wiki/Cell_wall" title="Cell wall">cell walls</a>. It inhibits cross-linkage between the linear <a href="/wiki/Peptidoglycan" title="Peptidoglycan">peptidoglycan</a> polymer chains that make up a major component of the cell wall of <a href="/wiki/Gram-positive" class="mw-redirect" title="Gram-positive">Gram-positive</a> bacteria.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup> </p><p>Flucloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a> routes. However, like <a href="/wiki/Methicillin" title="Methicillin">methicillin</a>, it is less potent than <a href="/wiki/Benzylpenicillin" title="Benzylpenicillin">benzylpenicillin</a> against non-β-lactamase-producing Gram-positive bacteria.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup> </p><p>Flucloxacillin has similar <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a>, antibacterial activity, and indications to dicloxacillin, and the two agents are considered interchangeable. It is reported to have higher, though rare, incidence of severe hepatic <a href="/wiki/Adverse_effect_(medicine)" class="mw-redirect" title="Adverse effect (medicine)">adverse effects</a> than dicloxacillin,<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> but a lower incidence of renal adverse effects.<sup id="cite_ref-AMH2006_23-4" class="reference"><a href="#cite_note-AMH2006-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=10" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Flucloxacillin is insensitive to <a href="/wiki/Beta-lactamase" title="Beta-lactamase">beta-lactamase</a> (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the <a href="/wiki/Isoxazole" title="Isoxazole">isoxazolyl</a> group on the <a href="/wiki/Side_chain" title="Side chain">side chain</a> of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side chain <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a>. Thus, it is able to bind to <a href="/wiki/Penicillin-binding_protein" class="mw-redirect" title="Penicillin-binding protein">penicillin-binding proteins</a> and inhibit peptidoglycan crosslinking, but is not bound by or inactivated by β-lactamases.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=11" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Flucloxacillin was developed in the 1960s following an increase in penicillin-resistant (<a href="/wiki/Beta-lactamase" title="Beta-lactamase">beta-lactamase</a> producing) staphylococcal infections due to the widespread use of <a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">benzylpenicillin</a> by 1960.<sup id="cite_ref-White2010_29-0" class="reference"><a href="#cite_note-White2010-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Page2012_30-0" class="reference"><a href="#cite_note-Page2012-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> All the natural penicillins and first semi-synthetic penicillins were destroyed by staphylococcal beta-lactamase, leading <a href="/wiki/Beecham_(pharmaceutical_company)" class="mw-redirect" title="Beecham (pharmaceutical company)">Beecham</a> (later <a href="/wiki/GlaxoSmithKline" class="mw-redirect" title="GlaxoSmithKline">GlaxoSmithKline</a>) to search for more stable antibiotics. By 1962, a series of similarly structured acid-stable penicillins (<a href="/wiki/Oxacillin" title="Oxacillin">oxacillin</a>, <a href="/wiki/Cloxacillin" title="Cloxacillin">cloxacillin</a>, <a href="/wiki/Dicloxacillin" title="Dicloxacillin">dicloxacillin</a> and flucloxacillin), with the potential for being taken by mouth, were developed. Flucloxacillin and dicloxacillin showed particular stability against the beta-lactamase enzyme of <i>Staph. aureus</i> and could withstand acid.<sup id="cite_ref-White2010_29-1" class="reference"><a href="#cite_note-White2010-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Page2012_30-1" class="reference"><a href="#cite_note-Page2012-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Beecham further developed cloxacillin and popularised flucloxacillin in the UK, while <a href="/wiki/Bristol_Laboratories" class="mw-redirect" title="Bristol Laboratories">Bristol Laboratories</a> concentrated on marketing oxacillin and dicloxacillin in the United States, leading to the difference in use in both countries.<sup id="cite_ref-Greenwood2008_31-0" class="reference"><a href="#cite_note-Greenwood2008-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sutherland_32-0" class="reference"><a href="#cite_note-Sutherland-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Flucloxacillin was first marketed in Europe in the 1970s.<sup id="cite_ref-Wu2011_8-3" class="reference"><a href="#cite_note-Wu2011-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Available_forms">Available forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=12" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Both the oral and intravenous preparations of flucloxacillin are inexpensive and are available as the sodium salt flucloxacillin sodium, in <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">capsules</a> (250 or 500 mg), oral <a href="/wiki/Suspension_(chemistry)" title="Suspension (chemistry)">suspensions</a> (125 mg/5 ml or 250 mg/5 ml), and injections (powder for reconstitution, 250, 500, 1000 and 2000 mg per vial).<sup id="cite_ref-Hitchings2015_5-4" class="reference"><a href="#cite_note-Hitchings2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EMC_33-0" class="reference"><a href="#cite_note-EMC-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Flucloxacillin is not commonly used in the United States or Canada as of 2011.<sup id="cite_ref-Wu2011_8-4" class="reference"><a href="#cite_note-Wu2011-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In several other countries however, it is supplied under a variety of trade names including Floxapen, Flopen, Flubex, Flupen, Phylopen, and Staphylex.<sup id="cite_ref-Drugs.com_1-1" class="reference"><a href="#cite_note-Drugs.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Combination">Combination</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=13" title="Edit section: Combination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Co-fluampicil" class="mw-redirect" title="Co-fluampicil">Co-fluampicil</a></div> <p>Flucloxacillin is combined with <a href="/wiki/Ampicillin" title="Ampicillin">ampicillin</a> in <a href="/wiki/Co-fluampicil" class="mw-redirect" title="Co-fluampicil">co-fluampicil</a>.<sup id="cite_ref-BNF80_6-15" class="reference"><a href="#cite_note-BNF80-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 196.66666666667px"> <div class="thumb" style="width: 194.66666666667px;"><span typeof="mw:File"><a href="/wiki/File:Flucloxacillin_powder_for_oral_solution.jpg" class="mw-file-description" title="Flucloxacillin powder for oral solution 125 mg/5ml, with measuring spoon"><img alt="Flucloxacillin powder for oral solution 125 mg/5ml, with measuring spoon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Flucloxacillin_powder_for_oral_solution.jpg/292px-Flucloxacillin_powder_for_oral_solution.jpg" decoding="async" width="195" height="260" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Flucloxacillin_powder_for_oral_solution.jpg/439px-Flucloxacillin_powder_for_oral_solution.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Flucloxacillin_powder_for_oral_solution.jpg/585px-Flucloxacillin_powder_for_oral_solution.jpg 2x" data-file-width="3024" data-file-height="4032" /></a></span></div> <div class="gallerytext">Flucloxacillin powder for oral solution 125 mg/5ml, with measuring spoon</div> </li> <li class="gallerybox" style="width: 196.66666666667px"> <div class="thumb" style="width: 194.66666666667px;"><span typeof="mw:File"><a href="/wiki/File:Flucloxacillin_preparations.jpg" class="mw-file-description" title="Selection of Flucloxacillin preparations found in the UK"><img alt="Selection of Flucloxacillin preparations found in the UK" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Flucloxacillin_preparations.jpg/292px-Flucloxacillin_preparations.jpg" decoding="async" width="195" height="260" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Flucloxacillin_preparations.jpg/439px-Flucloxacillin_preparations.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Flucloxacillin_preparations.jpg/585px-Flucloxacillin_preparations.jpg 2x" data-file-width="3024" data-file-height="4032" /></a></span></div> <div class="gallerytext">Selection of Flucloxacillin preparations found in the UK</div> </li> <li class="gallerybox" style="width: 266.66666666667px"> <div class="thumb" style="width: 264.66666666667px;"><span typeof="mw:File"><a href="/wiki/File:Co-fluampicil_capsules_and_container.jpg" class="mw-file-description" title="Co-fluampicil: Flucloxacillin combined with ampicillin (UK)"><img alt="Co-fluampicil: Flucloxacillin combined with ampicillin (UK)" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Co-fluampicil_capsules_and_container.jpg/397px-Co-fluampicil_capsules_and_container.jpg" decoding="async" width="265" height="260" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Co-fluampicil_capsules_and_container.jpg/596px-Co-fluampicil_capsules_and_container.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/Co-fluampicil_capsules_and_container.jpg/794px-Co-fluampicil_capsules_and_container.jpg 2x" data-file-width="2829" data-file-height="2778" /></a></span></div> <div class="gallerytext">Co-fluampicil: Flucloxacillin combined with ampicillin (UK)</div> </li> </ul> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flucloxacillin&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Drugs.com-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Drugs.com_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Drugs.com_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/flucloxacillin.html">"Flucloxacillin"</a>. <i>Drugs.com</i><span class="reference-accessdate">. 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.navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cell_wall_disruptive_antibiotics" title="Template:Cell wall disruptive antibiotics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cell_wall_disruptive_antibiotics" title="Template talk:Cell wall disruptive antibiotics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cell_wall_disruptive_antibiotics" title="Special:EditPage/Template:Cell wall disruptive antibiotics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_active_on_the_cell_wall_and_envelope_(J01C-J01D)931" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibacterials</a> active on the <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a> and <a href="/wiki/Cell_envelope_antibiotic" title="Cell envelope antibiotic">envelope</a> (<a href="/wiki/ATC_code_J01#J01C" title="ATC code J01">J01C</a>-<a href="/wiki/ATC_code_J01#J01D" title="ATC code J01">J01D</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Beta-lactam_antibiotics" class="mw-redirect" title="Beta-lactam antibiotics">β-lactams</a><br /><small><span class="nobold">(inhibit synthesis<br />of peptidoglycan<br />layer of bacterial<br />cell wall by binding<br />to and inhibiting<br /><a href="/wiki/Penicillin-binding_proteins" title="Penicillin-binding proteins">PBPs</a>, a group of<br /><a href="/wiki/DD-Transpeptidase" title="DD-Transpeptidase"><small>D</small>-alanyl-<small>D</small>-alanine<br />transpeptidases</a>)</span></small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Penicillin" title="Penicillin">Penicillins</a> (<a href="/wiki/Penam" title="Penam">Penams</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">Narrow<br />spectrum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">β-lactamase sensitive</a><br />(1st generation)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzylpenicillin" title="Benzylpenicillin">Benzylpenicillin (G)</a><sup>#</sup></li> <li><a href="/wiki/Benzathine_benzylpenicillin" title="Benzathine benzylpenicillin">Benzathine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Procaine_benzylpenicillin" title="Procaine benzylpenicillin">Procaine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Phenoxymethylpenicillin" title="Phenoxymethylpenicillin">Phenoxymethylpenicillin (V)</a><sup>#</sup></li> <li><a href="/wiki/Propicillin" title="Propicillin">Propicillin</a><sup>‡</sup></li> <li><a href="/wiki/Pheneticillin" title="Pheneticillin">Pheneticillin</a><sup>‡</sup></li> <li><a href="/wiki/Azidocillin" title="Azidocillin">Azidocillin</a><sup>‡</sup></li> <li><a href="/wiki/Clometocillin" title="Clometocillin">Clometocillin</a><sup>‡</sup></li> <li><a href="/wiki/Penamecillin" title="Penamecillin">Penamecillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#β-lactamase-resistant" title="List of β-lactam antibiotics">β-lactamase resistant</a><br />(2nd generation)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cloxacillin" title="Cloxacillin">Cloxacillin</a><sup>#</sup> (<a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a class="mw-selflink selflink">Flucloxacillin</a>)</li> <li><a href="/wiki/Oxacillin" title="Oxacillin">Oxacillin</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Methicillin" title="Methicillin">Methicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Extended-spectrum_penicillin" title="Extended-spectrum penicillin">Extended<br />spectrum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminopenicillin" title="Aminopenicillin">Aminopenicillins</a> (3rd generation)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amoxicillin" title="Amoxicillin">Amoxicillin</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin" title="Ampicillin">Ampicillin</a><sup>#</sup> (<a href="/wiki/Pivampicillin" title="Pivampicillin">Pivampicillin</a></li> <li><a href="/wiki/Hetacillin" title="Hetacillin">Hetacillin</a><sup>‡</sup></li> <li><a href="/wiki/Bacampicillin" title="Bacampicillin">Bacampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Lenampicillin" title="Lenampicillin">Lenampicillin</a></li> <li><a href="/wiki/Metampicillin" title="Metampicillin">Metampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Talampicillin" title="Talampicillin">Talampicillin</a><sup>‡</sup>)</li> <li><a href="/wiki/Epicillin" title="Epicillin">Epicillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carboxypenicillin" title="Carboxypenicillin">Carboxypenicillins</a> (4th generation)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ticarcillin" title="Ticarcillin">Ticarcillin</a></li> <li><a href="/wiki/Carbenicillin" title="Carbenicillin">Carbenicillin</a><sup>‡</sup> / <a href="/wiki/Carindacillin" title="Carindacillin">Carindacillin</a><sup>‡</sup></li> <li><a href="/wiki/Temocillin" title="Temocillin">Temocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ureidopenicillin" title="Ureidopenicillin">Ureidopenicillins</a> (4th generation)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Piperacillin" title="Piperacillin">Piperacillin</a></li> <li><a href="/wiki/Azlocillin" title="Azlocillin">Azlocillin</a><sup>‡</sup></li> <li><a href="/wiki/Mezlocillin" title="Mezlocillin">Mezlocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mecillinam" title="Mecillinam">Mecillinam</a> (<a href="/wiki/Pivmecillinam" title="Pivmecillinam">Pivmecillinam</a>)</li> <li><a href="/wiki/Sulbenicillin" title="Sulbenicillin">Sulbenicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbapenem" title="Carbapenem">Carbapenems</a> / <a href="/wiki/Penem" title="Penem">Penems</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Carbapenems (<a href="/wiki/Ertapenem" title="Ertapenem">Ertapenem</a></li> <li><a href="/wiki/Antipseudomonal" class="mw-redirect" title="Antipseudomonal">Antipseudomonal</a> (<a href="/wiki/Doripenem" title="Doripenem">Doripenem</a></li> <li><a href="/wiki/Imipenem" title="Imipenem">Imipenem</a></li> <li><a href="/wiki/Meropenem" title="Meropenem">Meropenem</a>)</li> <li><a href="/wiki/Biapenem" title="Biapenem">Biapenem</a><sup>‡</sup></li> <li><a href="/wiki/Panipenem" title="Panipenem">Panipenem</a>)</li> <li>Penems (<a href="/wiki/Faropenem" title="Faropenem">Faropenem</a></li> <li><a href="/wiki/Ritipenem" title="Ritipenem">Ritipenem</a><sup>§</sup></li> <li><a href="/wiki/Sulopenem" title="Sulopenem">Sulopenem</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephem" title="Cephem">Cephems</a><br /><a href="/wiki/Cephalosporin" title="Cephalosporin">Cephalosporins</a><br /><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycins</a><br /><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephems</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#First_generation" title="Cephalosporin">1st generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefazolin" title="Cefazolin">Cefazolin</a><sup>#</sup></li> <li><a href="/wiki/Cefalexin" title="Cefalexin">Cefalexin</a> <sup>#</sup></li> <li><a href="/wiki/Cefadroxil" title="Cefadroxil">Cefadroxil</a></li> <li><a href="/wiki/Cefapirin" title="Cefapirin">Cefapirin</a></li> <li><a href="/wiki/Cefazedone" title="Cefazedone">Cefazedone</a><sup>‡</sup></li> <li><a href="/wiki/Cefazaflur" title="Cefazaflur">Cefazaflur</a><sup>‡</sup></li> <li><a href="/wiki/Cefradine" title="Cefradine">Cefradine</a><sup>‡</sup></li> <li><a href="/wiki/Cefroxadine" title="Cefroxadine">Cefroxadine</a><sup>‡</sup></li> <li><a href="/wiki/Ceftezole" title="Ceftezole">Ceftezole</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloglycin" title="Cefaloglycin">Cefaloglycin</a><sup>‡</sup></li> <li><a href="/wiki/Cefacetrile" title="Cefacetrile">Cefacetrile</a><sup>‡</sup></li> <li><a href="/wiki/Cefalonium" title="Cefalonium">Cefalonium</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloridine" class="mw-redirect" title="Cefaloridine">Cefaloridine</a><sup>‡</sup></li> <li><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a></li> <li><a href="/wiki/Cefatrizine" title="Cefatrizine">Cefatrizine</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Second_generation" title="Cephalosporin">2nd generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefaclor" title="Cefaclor">Cefaclor</a></li> <li><a href="/wiki/Cefprozil" title="Cefprozil">Cefprozil</a></li> <li><a href="/wiki/Cefuroxime" title="Cefuroxime">Cefuroxime</a></li> <li><a href="/wiki/Cefuroxime_axetil" title="Cefuroxime axetil">Cefuroxime axetil</a></li> <li><a href="/wiki/Cefamandole" title="Cefamandole">Cefamandole</a><sup>‡</sup></li> <li><a href="/wiki/Cefonicid" title="Cefonicid">Cefonicid</a><sup>‡</sup></li> <li><a href="/wiki/Ceforanide" title="Ceforanide">Ceforanide</a><sup>‡</sup></li> <li><a href="/wiki/Cefuzonam" title="Cefuzonam">Cefuzonam</a><sup>‡</sup></li> <li><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycin</a> (<a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a></li> <li><a href="/wiki/Cefotetan" title="Cefotetan">Cefotetan</a></li> <li><a href="/wiki/Cefminox" title="Cefminox">Cefminox</a><sup>‡</sup></li> <li><a href="/wiki/Cefbuperazone" title="Cefbuperazone">Cefbuperazone</a><sup>‡</sup></li> <li><a href="/wiki/Cefmetazole" title="Cefmetazole">Cefmetazole</a><sup>‡</sup>)</li> <li><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephem</a> (<a href="/wiki/Loracarbef" title="Loracarbef">Loracarbef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Third_generation" title="Cephalosporin">3rd generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefixime" title="Cefixime">Cefixime</a><sup>#</sup></li> <li><a href="/wiki/Ceftriaxone" title="Ceftriaxone">Ceftriaxone</a><sup>#</sup></li> <li><a href="/wiki/Cefotaxime" title="Cefotaxime">Cefotaxime</a><sup>#</sup></li> <li>Antipseudomonal (<a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a><sup>#</sup></li> <li><a href="/wiki/Cefoperazone" title="Cefoperazone">Cefoperazone</a>)</li> <li><a href="/wiki/Cefdinir" title="Cefdinir">Cefdinir</a></li> <li><a href="/wiki/Cefcapene" title="Cefcapene">Cefcapene</a></li> <li><a href="/wiki/Cefdaloxime" title="Cefdaloxime">Cefdaloxime</a></li> <li><a href="/wiki/Ceftizoxime" title="Ceftizoxime">Ceftizoxime</a></li> <li><a href="/wiki/Cefmenoxime" title="Cefmenoxime">Cefmenoxime</a></li> <li><a href="/wiki/Cefpiramide" title="Cefpiramide">Cefpiramide</a></li> <li><a href="/wiki/Cefpodoxime" title="Cefpodoxime">Cefpodoxime</a></li> <li><a href="/wiki/Ceftibuten" title="Ceftibuten">Ceftibuten</a></li> <li><a href="/wiki/Cefditoren" title="Cefditoren">Cefditoren</a></li> <li><a href="/wiki/Cefotiam" title="Cefotiam">Cefotiam</a><sup>‡</sup></li> <li><a href="/wiki/Cefetamet" title="Cefetamet">Cefetamet</a><sup>‡</sup></li> <li><a href="/wiki/Cefodizime" title="Cefodizime">Cefodizime</a><sup>‡</sup></li> <li><a href="/wiki/Cefpimizole" title="Cefpimizole">Cefpimizole</a><sup>‡</sup></li> <li><a href="/wiki/Cefsulodin" title="Cefsulodin">Cefsulodin</a><sup>‡</sup></li> <li><a href="/wiki/Cefteram" title="Cefteram">Cefteram</a><sup>‡</sup></li> <li><a href="/wiki/Ceftiolene" title="Ceftiolene">Ceftiolene</a><sup>‡</sup></li> <li><a href="/wiki/Oxacephem" title="Oxacephem">Oxacephem</a> (<a href="/wiki/Flomoxef" title="Flomoxef">Flomoxef</a></li> <li><a href="/wiki/Latamoxef" title="Latamoxef">Latamoxef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fourth_generation" title="Cephalosporin">4th generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefepime" title="Cefepime">Cefepime</a></li> <li><a href="/wiki/Cefozopran" title="Cefozopran">Cefozopran</a><sup>‡</sup></li> <li><a href="/wiki/Cefpirome" title="Cefpirome">Cefpirome</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fifth_generation" title="Cephalosporin">5th generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ceftaroline_fosamil" title="Ceftaroline fosamil">Ceftaroline fosamil</a></li> <li><a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a></li> <li><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Siderophore" title="Siderophore">Siderophore</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefiderocol" title="Cefiderocol">Cefiderocol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">Veterinary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ceftiofur" title="Ceftiofur">Ceftiofur</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a></li> <li><a href="/wiki/Cefovecin" title="Cefovecin">Cefovecin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monobactam" title="Monobactam">Monobactams</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aztreonam" title="Aztreonam">Aztreonam</a></li> <li><a href="/wiki/Tigemonam" title="Tigemonam">Tigemonam</a><sup>‡</sup></li> <li><a href="/wiki/Carumonam" title="Carumonam">Carumonam</a><sup>‡</sup></li> <li><a href="/wiki/Nocardicin_A" title="Nocardicin A">Nocardicin A</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%92-Lactamase_inhibitor" title="Β-Lactamase inhibitor">β-lactamase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Penam" title="Penam">Penam</a> (<a href="/wiki/Sulbactam" title="Sulbactam">Sulbactam</a></li> <li><a href="/wiki/Tazobactam" title="Tazobactam">Tazobactam</a>)</li> <li><a href="/wiki/Clavam" title="Clavam">Clavam</a> (<a href="/wiki/Clavulanic_acid" title="Clavulanic acid">Clavulanic acid</a>)</li> <li>non-β-lactam (<a href="/wiki/Avibactam" title="Avibactam">Avibactam</a></li> <li><a href="/wiki/Durlobactam" title="Durlobactam">Durlobactam</a></li> <li><a href="/wiki/Relebactam" title="Relebactam">Relebactam</a></li> <li><a href="/wiki/Vaborbactam" title="Vaborbactam">Vaborbactam</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Amoxicillin/clavulanic acid</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin/flucloxacillin" title="Ampicillin/flucloxacillin">Ampicillin/flucloxacillin</a></li> <li><a href="/wiki/Ampicillin/sulbactam" title="Ampicillin/sulbactam">Ampicillin/sulbactam</a> (<a href="/wiki/Sultamicillin" title="Sultamicillin">Sultamicillin</a>)</li> <li><a href="/wiki/Aztreonam/avibactam" title="Aztreonam/avibactam">Aztreonam/avibactam</a></li> <li><a href="/wiki/Benzathine_benzylpenicillin/procaine_benzylpenicillin" title="Benzathine benzylpenicillin/procaine benzylpenicillin">Benzathine benzylpenicillin/procaine benzylpenicillin</a></li> <li><a href="/wiki/Cefepime/enmetazobactam" title="Cefepime/enmetazobactam">Cefepime/enmetazobactam</a></li> <li><a href="/wiki/Cefoperazone/sulbactam" title="Cefoperazone/sulbactam">Cefoperazone/sulbactam</a></li> <li><a href="/wiki/Ceftazidime/avibactam" title="Ceftazidime/avibactam">Ceftazidime/avibactam</a></li> <li><a href="/wiki/Ceftolozane/tazobactam" title="Ceftolozane/tazobactam">Ceftolozane/tazobactam</a></li> <li><a href="/wiki/Imipenem/cilastatin" title="Imipenem/cilastatin">Imipenem/cilastatin</a><sup>#</sup></li> <li><a href="/wiki/Imipenem/cilastatin/relebactam" title="Imipenem/cilastatin/relebactam">Imipenem/cilastatin/relebactam</a></li> <li><a href="/wiki/Meropenem/vaborbactam" title="Meropenem/vaborbactam">Meropenem/vaborbactam</a></li> <li><a href="/wiki/Panipenem/betamipron" title="Panipenem/betamipron">Panipenem/betamipron</a></li> <li><a href="/wiki/Piperacillin/tazobactam" title="Piperacillin/tazobactam">Piperacillin/tazobactam</a></li> <li><a href="/wiki/Sulbactam/durlobactam" title="Sulbactam/durlobactam">Sulbactam/durlobactam</a></li> <li><a href="/wiki/Sulopenem/probenecid" title="Sulopenem/probenecid">Sulopenem/probenecid</a></li> <li><a href="/wiki/Ticarcillin/clavulanic_acid" title="Ticarcillin/clavulanic acid">Ticarcillin/clavulanic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipopeptide" title="Lipopeptide">Lipopeptides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Insert into bacterial cell wall causing perforation and depolarization: <a href="/wiki/Daptomycin" title="Daptomycin">Daptomycin</a></li> <li><a href="/wiki/Surfactin" title="Surfactin">Surfactin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibits PG elongation and crosslinking: <a href="/wiki/Ramoplanin" title="Ramoplanin">Ramoplanin</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibit <a href="/wiki/Peptidoglycan" title="Peptidoglycan">PG</a> subunit synthesis and transport: <a href="/wiki/N-Acetylmuramic_acid" title="N-Acetylmuramic acid">NAM</a> synthesis inhibition (<a href="/wiki/Fosfomycin" title="Fosfomycin">Fosfomycin</a>)</li> <li><a href="/wiki/D-alanine%E2%80%94D-alanine_ligase" title="D-alanine—D-alanine ligase">DADAL</a>/<a href="/wiki/Alanine_racemase" title="Alanine racemase">AR</a> inhibitors (<a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a>)</li> <li><a href="/wiki/Bactoprenol" title="Bactoprenol">bactoprenol</a> inhibitors (<a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Hydrolyze NAM-NAG <ul><li><a href="/wiki/Lysozyme" title="Lysozyme">lysozyme</a></li></ul></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a> <ul><li><a href="/wiki/Gramicidin" title="Gramicidin">Gramicidin</a></li> <li><a href="/wiki/Tyrocidine" title="Tyrocidine">Tyrocidine</a></li></ul></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a><sup>#</sup></li> <li><a href="/wiki/Teixobactin" title="Teixobactin">Teixobactin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Xenobiotic-sensing_receptor_modulators953" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators953" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Constitutive androstane receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Pregnane X receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ<sup>4</sup>-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ<sup>5</sup>-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ<sup>5</sup>-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a class="mw-selflink selflink">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum"><i>Hypericum perforatum</i> (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">γ-Linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 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